ChemicalBook CAS DataBase List METHYLPHENYLSELENIDE

METHYLPHENYLSELENIDE synthesis

11synthesis methods

Product Name:METHYLPHENYLSELENIDE
CAS Number:4346-64-9
Molecular formula:C7H8Se
Molecular Weight:171.1

591-50-4 Synthesis

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Yield:4346-64-9 100 %Chromat.

Reaction Conditions:

Stage #1: iodobenzenewith selenobenzamide;potassium tert-butylate in dimethyl sulfoxide; for 3 h;Inert atmosphere;Irradiation;
Stage #2: methyl iodide in dimethyl sulfoxide;Inert atmosphere;

Steps:

Representative experimental procedure:

The photochemical reaction was carried out in a three-necked, 10 mL Schlenk tube equipped with a nitrogen gas inlet and a magnetic stirrer. The flask was dried under vacuum, filled with nitrogen and then charged with 10 mL of dried DMSO. 3.75 mmol of tert-BuOK for selenobenzamide (3.25 mmol for anion selenourea and 2.5 mmol for KSeCN) was added to the degassed DMSO under nitrogen, then 2.5 mmol of the nucleophile 1-3 and 0.5 mmol of ArX were added to the reaction mixture. After 3 h of irradiation with a high-pressure Hg lamp, the reaction was quenched by the addition of MeI (6 equiv) in excess and 30 mL of water, and the mixture was then extracted with dichloromethane (3 × 20 mL). The organic extract was washed twice with water, dried and the products were quantified by GC with diphenyl diselenide as internal standard.

References:

Bouchet, Lydia M.;Pe?é?ory, Alicia B.;Argüello, Juan E. [Tetrahedron Letters,2011,vol. 52,# 9,p. 969 - 972] Location in patent:experimental part